The Tired Entrepreneur: The challenges of rebuilding unstoppable momentum

23 May 2017 by Allan King

“Enduring success and growth for any business today is dependent on building and maintaining unstoppable momentum” Michael McQueen

I have owned and operated my own business for nearly 18 years. During this period, we have seen solid and extended growth. With this growth has come commensurate success. As a company, we were recognised by industry as a leader and acknowledged by our partners at a local, national and global level. We always operated under the mantra of ‘what we do, we do well. What we don’t do, we don’t do.’

Three years ago, things changed. I don’t mean the growth or the success. We continued to post results that defied market trends. It changed because I called the ball on our existing model. I came to realise that cloud represented the next big opportunity, but also a threat that had the potential to disrupt all that we had built.

So began the long hard road of change and all the challenges that came with trying to teach an old dog new tricks. I write this hoping that it may help others accelerate their own change agenda, and just maybe, side step a few of the more challenging issues I encountered along the way.

1. The Weight of Expectation

Boy, oh boy, did I underestimate the loneliness of the journey. I can honestly say I would prefer to spin-up another start-up before attempting to change the culture and direction of a mature, successful business. Why? Firstly, very few people understood the need for change. Remember, we were still growing our traditional lines of business. Cloud was viewed as ‘cool’ but not a strategy for the Enterprise.. Many felt that Government, our largest vertical, would never transition to cloud as they had ‘unique’ security requirements. If they did, it would be a slow laborious adoption. I was more aggressive in my assumptions. Turns out both sides were wrong. It was happening much quicker than anyone expected!

With the momentum of cloud building, and many of our customers actively pursuing a cloud first strategy, staff eventually turned their attention to our new and emerging strategy. What did it mean to them? How would we compete? Where we going to be able to differentiate as we had in the past? Would it effect my bonus? How can I achieve my OTE? Was it the right strategy? Why was it taking so long? The questions kept coming. The pressure to execute kept mounting. And the elephant in the room? How were we going to succeed when so many well-funded multinationals and vendors hadn’t?

The pressure of expectation was exhausting! Change is not for the faint of heart, but if you truly believe in your vision, you can prevail – in time 🙂

2. Make Change, Make Enemies

Woodrow Wilson once stated that “if you want to make enemies, try to change something.” We encountered this almost immediately. We have always been transparent with our partners. We have been loyal, focused and successful with some of the largest vendors in the industry. However, when we outlined our future direction, we had to face off against senior management whose attitudes ranged from passive aggressive to outright hostile. Why? Because we were no longer 100% aligned with their strategy, even though their strategy was unresolved and in most cases embryonic. There was an expectation that we would simply wait and align behind their vision ONCE it was better defined. To do otherwise was to be branded a disloyal partner.

But we couldn’t afford to wait. Right or wrong we needed to move quickly. We needed to embrace emerging markets with the same energy and focus that had served us so well in the past. We had spent over nine months researching cloud and engaging customers to understand their needs for the new era. We knew we had to forge new partnerships. Even though it caused us a lot of pain in the process, but it was the right thing to do.

As the market started to shake out, and the emerging vendors began to assume an indomitable position, attitudes started to soften. Many even grudgingly acknowledged our strategy as ‘insightful’ and ‘compelling’ – but we had inevitably lost ground with our traditional vendor base that would never be reclaimed.

3. Organisational Whiplash

Communication is the cornerstone of a transformation agenda. But be very aware of organisational whiplash. If I learned one lesson over the past three years, it would be to over communicate the ‘Why’ and not the ‘What’.

We defined early in the process the Why. It was the foundation of everything we did. Every investment we made. We had a singular focus with the drive to execute. But along the way I assumed too much. I assumed everyone was on board with the vision. They weren’t. I had presented it many times, but it just didn’t stick the way I had expected.

When building and executing a new strategy, you ultimately discard more than you retain. We were operating in a nascent market trying to determine the best approach to deliver the outcomes as defined by our customers. We had also mapped a number of technical and operational challenges that we knew we had to solve. This resulted in a lot of water cooler type conversations. A lot of R&D was expended testing and often discarding ideas and partner products. It was inevitable as the market (the so called API economy) we were engaged with was very immature.

What we didn’t foresee was the effect this had on the periphery. We operate in a large open plan office. The relentless ‘fail fast’ process was viewed as ‘lurching’ from one idea to the next. The perception was we didn’t have a strategy, when quite the opposite was the case. We knew exactly what we wanted to achieve but we needed to test the veracity of the marketing as many products over promised and under delivered.

4. The ‘Glory’ Hires

Don’t confuse the term ‘Glory’ with your top performers. I use it to differentiate between those that helped you build the business and those that joined you in the Glory Days – when your brand is strong and momentum fills your sails. During this period, morale is at its highest and everyone feels empowered.

Now, don’t get me wrong, these hires are a natural and critical part of business growth, but you must be aware that their motivations for joining you may differ from your long term hires. They may not be interested in getting dirty with ‘what’s next’ just because you ask. They joined to be part of something great, not build it. So when your core offering is being disrupted and you need to aggressively change direction, don’t be surprised when a few of these late hires leave. It’s inevitable, but not personal. You can’t afford to view it as such and just remember that everyone contributes in their own way. Not everyone is motivated by the need to rebuild, which can often be difficult and frustrating with less visible and immediate benefits.

5. Gamification

The prospect of change is confronting, in particular to engineers who have dedicated their entire working career developing niche skills. Why? Because many of these skills are being commoditised or moved to cloud. Take O365 as a great example. This transition to an online service can quickly render over 20 years’ experience in Microsoft Exchange obsolete. The need to stay in school, to reinvent oneself had never been greater and yet many of my best engineers continued as if it was business as usual, seemingly waiting for change to overtake them.

This was the most frustrating part of the journey. But one we had to address with singular focus. We had to find a way to engage with our best people or wither and die due to a lack of relevant skills. To combat this, we Gamified the learning process.

We Gamified the learning process by developing a series of challenges that ran over a 10-week period. Each week the challenge (kept small to encourage participation) was evaluated and a small cash prize was awarded (first and second). To ensure ongoing commitment, we used the previous week’s output as the foundation for the coming weeks challenge. It was a great way to get the competitive juices flowing, but also encourage participation and knowledge sharing. The ultimate winner was gifted something notable, something worth the time and effort required to complete all ten weeks.

As a side note, we didn’t limit these events to purely technical topics. We wanted to engage and encourage non-technical staff as well. In fact, our fitness challenge, run initially over 12 weeks, is still running today (without the incentives) nearly three years later.

6. New Blood. New thoughts. New Opportunities.

If you ask any avid gardener, they will tell you the most daunting part of maintaining a beautiful garden is to know when to hack-into (a term borrowed from my father, whom, by the way, was not an avid gardener) a tree, bush or plant in full bloom. It is always tempting to wait a little longer and avoid cutting something back. But without the right care, which can often leave your favourite tree in an unsightly state, it will fail to bloom in the coming seasons.

This was, perhaps, the most difficult lesson I learnt during the transition. I realised that we needed new skills and new thinking if we were to rebuild the unstoppable momentum we had enjoyed in the past. This wasn’t a conscious process. It was very much an organic result. The team was struggling to build momentum, and I fretted. I gave authority and responsibility but the past was holding us back. It wasn’t until we lost a few senior members and introduced a new crop of leaders that I realised what was missing – a passion for ‘what could be’ versus ‘what was’. A complete and unbiased approach to building something great again!

I hope that you found this article useful, but, if not, at least a little bit thought provoking. I don’t know why I felt compelled to write it. Perhaps, I hoped it would be cathartic? Perhaps it was. Time will tell.

Post by Allan King

Allan King is the Founder and Managing Director of Buttonwood, an Australian startup that wants to transform the way enterprises build and secure hybrid cloud services without unnecessary cost or complexity.